


Round the USA Romance

by Ldrmaslaz248



Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe - Modern Setting, Alternate Universe- No Supernatural, Anna and Castiel are friends, Bisexual Dean Winchester, Cas works in the Library, Castiel is a Novak, Charlie is alive, Dean and Meg are friends, Liberian Castiel, M/M, Tacky Hawaiian Shirts, Travel Agent Dean, halloween party time, mentions of John's crap parenting
Language: English
Status: Completed
Published: 2017-12-04
Updated: 2017-12-04
Packaged: 2019-02-10 11:38:00
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,308
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12911139
Author URL: https://archiveofourown.org/users/Ldrmaslaz248/pseuds/Ldrmaslaz248
Summary: You know when you are having one of those days. You know the kind. You just wake up and immediately know that things just aren’t going to go your way. Everything that can go wrong is going to go wrong. Then you fall back into your bed at the end of it all flabbergasted on why you even left it that morning to begin with. Well let’s just say that our dear Castiel was having one of those days, at least as far as the morning was concerned. Everything was going wrong for our sweet Liberian.Dean's a Travel Agent and Cas is going on his first vacation. Will the two find love along the way?





	1. Chapter 1

You know when you are having one of those days. You know the kind. You just wake up and immediately know that things just aren’t going to go your way. Everything that can go wrong is going to go wrong. Then you fall back into your bed at the end of it all flabbergasted on why you even left it that morning to begin with. Well let’s just say that our dear Castiel was having one of those days, at least as far as the morning was concerned. Everything was going wrong for our sweet Liberian. 

Castiel worked at the Central Branch of the Kansas City Public Library. He was mainly known to be found in the children’s section, but he had all kinds of jobs all over the building. It was more like his coworkers pleaded and begged him for his help so much until he couldn’t say no. His inability to utter the two-letter word is what got him into this predicament this morning. 

Last week had been his 20th anniversary of working at the library. He had started working there when he had turned 16. Anyway, for his gift his coworkers, aka his friends, had all pitched in to give him a vacation so he would finally use his vacation days. Vacation days that, if they were psychical objects, would be covered in cobwebs and dust from never once being touched. 

He had wanted to decline but he hadn’t won the argument and so agreed to his tropical trip to Florida. Before he had to leave he had to finalize his travel plans with the travel agency that his friends had also hired. This agency was where he was now in a rush to get to on this no good, very bad morning. 

He had forgotten to set his alarm since he had come home very late last night. He overslept without his alarm so instead of having all morning to get ready to meet this Mr. Winchester he had only approximately 15 minutes. The coffee pot decided it was its day to die so the machine refused to grace him with a cup of coffee. It was supposed to be laundry day which, again, he didn’t realize was today on account it had been a stressful week at work. This meant he had only one item in his closet that he grabbed and slipped on with febreezed soaked pants and his reliable trench coat. 

He hoped into his car with only five minutes to get to the agency without being late. If there was one thing Castiel was it was never late. He despised the idea of being late and truly had a major fear of it. The yoga sandals that covered his feet hit the gas only for him to realize he only had enough in his tank to get to where he was going. 

Then finally he waltzed in the agency waiting room just as his time had run out. He nearly broke every traffic law to get there on time but he hadn’t been pulled over so that was at least the silver lining of the morning. While catching his breath, he spotted the little coffee machine for customers. He was about to reach out to it but a door opened to his left and a man stepped into the room. 

“Castiel Novak?”

“Um…yes.” 

The man smiled in greeting. “Good afternoon, welcome to Round the World Travel Agency, I’ll take you back to see Mr. Winchester.” 

Castiel nodded and followed the man down a small hallway. 

“My name is Aaron. This is Mr. Winchester’s office here.” Aaron went on after leading him into a good sized office before gesturing him to sit in the seat in front of a desk. 

“Is there anything I can get you? Mr. Winchester will be in a moment?” 

Castiel meekly asked for a simple cup of coffee to which Aaron nodded before leaving him alone in the room. He cast a glance around the office with small smile. It wasn’t as bare as he thought it was going to be, but it wasn’t overly decorated either. The decorations mostly were pleasant pictures of places around the world. Some were famous tourist spots while others were of places that appeared to be hidden gems. 

Castiel turned away from the frames as the office door began to turn. When it opened and the other man stepped in as they both caught eyes with each other they froze in surprise. 

“Cas?”

“Dean?” 

They both asked one after the other in confusion. Cas could only stare owlishly as in answer while Dean chuckled and closed his door. 

“Hey man, what are you doing here?” 

“Um…um…I-”

“Wait, I have an appointment with a…” Dean started as he sat behind his desk and opened the folder upon it. “…Castiel Novak? That’s you?”

“Ye-Yes.” Cas nodded as he finally shook off his surprise. 

“Whew, that’s a mouthful, but at least I now know where the ‘Cas’ is from,” Dean chuckled, “Wait, where does Meg get Clarence out of Castiel?” 

Cas blushed deeply and rubbed at the back of his neck shyly. He had forgotten that Meg had said that name in front of Dean on occasion. Cas and Dean had met each other through two of Cas’s friends; Anna and Meg. Anna had once dated Dean, though it hadn’t worked out, and they remained friends. He still had no clue to this day on how Dean and Meg became friends. 

Anna and Meg started to bring Dean with them to the parties that the library would throw every month or so. He also came to a couple of the karaoke nights that Cas’ friends dragged him too. Cas had never learned Dean’s last name because after they were first introduced Cas said his pleasantries but tried to avoid Dean with all the skill he could muster. 

He did this because he had quickly developed a crush on the blonde man after the first time he ever saw him. 

There were very few people who knew Cas was gay. Dean Winchester; the more he thought of the name the more he found it fit the man, was the most gorgeous person Castiel had ever laid eyes on. When after they met he had asked an occasional question about Dean to Anna and Meg and they, being his closest of close friends could instantly tell he liked the man. They were even faster on trying to set him up with Dean but thankfully he was somehow able to shut that down and made them drop the idea forever. 

He was perfectly okay with a one-sided crush. He didn’t need anything else though now sitting in the room with said crush was making Cas fidget. “My name…Castiel is the name of an angel, so when she found that out she started calling me the angel from ‘It’s a Wonderful Life.’” 

Dean laughed and nodded in acknowledgement. “Right! Sam made me watch that one time and still puts it on during Christmas. Well don’t worry, I’ll stick with Cas.” 

“I appreciate it.” Cas smiled in thankfulness to which Dean smiled back. 

“Awesome. Alright, so we’re going over the remaining details for your Florida trip in three weeks, correct?” 

“Yes.” 

“Well it looks you jumped ahead of schedule and are already ready.” Dean’s smile melted into a smirk and his tone practically purred in a flirtatious purr. Cas merely tilted his head in confusion to the change of speech and to the statement. 

Dean only smirked wider as his eyes raked up and down of what he could see over his desk. Cas looked down only to then blush crimson once more as he suddenly recalled his attire. He had been so surprised by Dean that the horribleness of the morning had all but vanished from his thoughts including what he was forced to wear. 

The shirt he had on was one he never wore on a regular occasion. He had truly only kept it for it had been a birthday present from Meg a couple years back. Cas glanced down at the brightly aqua colored Hawaiian shirt that had bright white tropical palm leaves upon it in a scattered manor. As he gave the offending item a small glare, he contemplated on why he even kept the gag gift and if he could have gotten away with a shirt at the top of his laundry basket. One with coffee stains perhaps, since that would have been fair less embarrassing and easier to explain. 

“Um…no…um…I mean, it was laundry day today so this was all I had.” 

“Oh gotcha!” Dean chuckled with an understanding nod. “I hate laundry day myself but don’t worry, that shirt looks good on ya. You should wear it on your trip. It’s perfect for the weather you’ll be having.” 

“I’ll be sure to pack it then.” Cas replied as he tried to not let the fact that Dean had just outright complimented him bring back his blush in full force. 

“Cool. Let’s get these details sorted then!” 

Aaron had delivered their drinks as they went over everything and they chatted about the final arrangements. Dean printed out sheets of maps, Cas’s travel information, and advice of top rated restaurants in the area where he would be staying, how to pack, etc. He sorted it in a folder and smiled up at Cas again. 

“Awesome, you’re all set. You and whoever you’re going with will have an awesome time if you follow what’s in here.” 

“Thank you though I’m not going with anyone.” 

“Seriously?” Dean asked, pausing in handing over the folder. 

“Well, yes. My friends are all covering my shifts the week of the trip, so obviously, they cannot come. I believe that was part of their gift. They are though all conspiring together to group call me each day to make sure I am actually getting out of the hotel and also not ‘burrowing myself in the Florida library.’” 

Dean chuckled as Cas had used literal air quotes while he spoke before dropping the folder back down on the desk between them. “So you’re really going to Florida by yourself for a week? That sounds like a torture more than a gift.” 

“I disagree. They did a lot to give this to me, so despite it being my first vacation, I will enjoy it, whether I am by myself or not.” 

“Wait, wait back up. First vacation? As in first vacation ever?”

“Yes.” Cas answered in confusion accompanied by another of his curious head tilts. 

“You have never once had a vacation?” 

“That’s right.” 

“The hell, man?” When Cas only frowned deeper in confusion, Dean continued. “How is it you never had a vacation?” 

“Well,” Cas began as he leaned back in the uncomfortable office chair. He knew he really didn’t owe Dean an explanation but at the same time it would hurt neither of them to answer the question honestly. 

“My family has always been very large. We did have the money to go wherever we liked but my parents were never ones to take us anywhere. They wanted us to focus more on shoving lessons down our throats. Learn about the world instead of go out and experience it, if you will. And since it was always that way, as soon as I could, I started working at the library since it was the one way I could get away from their constant supervision. Never really had the desire to do otherwise since then.” 

Dean was surprised but nodded in understanding. 

His dad had been like that. His dad enforced a “his way or the highway” kind of living and it was something Dean quickly became sick of. It had been Dean’s inspiration for becoming a travel agent. He couldn’t fly to save his life but to see wherever he could get to by car had been a dream come true, so he made sure to make the dream possible for others.   
He smiled as he then handed the packet to Cas before standing up. Cas raised from the chair he had been in and they both shook hands. Cas ignored his brain that could only think of what an amazing grip Dean had. 

“Well, then for a first vacation, you’re going to have a great time.” Dean encouraged as he came around the desk, walking with Cas to the door. 

“Thank you for you time, Dean. I appreciated it.” Cas replied with an encouraging smile of his own before nodding a final goodbye and left the building. If Dean watched Cas drive away from his office window, well, Cas didn’t need to know. 

 

To Be Continued...


	2. Chapter 2

“Dean?” Cas whispered as he watched the bowed leg god saunter up to him. It was a definite shock to see him. In Florida…in the same restaurant that Cas happened to be in. 

“Hi there, don’t I know you?” Dean asked in a casual tone yet there was definitely a teasing undertone. 

“What are you doing here?” Cas asked hesitatingly as he glanced down at his lap and messed with the silverware. His hands were shaking so he needed to occupy them. Dean full out laughed as he fell into the unoccupied chair across from Castiel and slid off his sunglasses. 

“Hello to you too, Cas.” Cas sighed and stopped fiddling with everything within reach. He raised his eyes to the emeralds across from him.

“You surprised me…” Cas confessed as he clutched his fists under the table. “…I don’t quite understand how you found me.” 

“Well I gotta admit that I asked Charlie for where I might find you. Not to mention you and I put your vacation together so I know the general area on where you were going to be.” Dean answered shyly before asking for water when the waitress came by the table. When she was once again gone, Cas had regained his confidence. 

“That’s not exactly what I mean, Dean.” He commented with his usual squinty face that Dean secretly loved. 

“Yeah, I know. It’s just that your itinerary looked like so much fun, so I figured I could come share some of that with you.” Cas didn’t comment only narrowed his eyes more as if to analyze every word. 

Dean just assumed Cas knew he was reading straight through his partial lie so he sighed. He crossed his arms settling them on the table. 

“Alright, alright. I came because no one should go on a vacation alone. The best parts of vacations are unwinding and being free with friends and family. I…I figured we were close enough friends, so it would be alright. Plus, I could show you the best time since it’s my job to know this place.” Cas was truly surprised and he couldn’t help blushing. 

He knew he usually avoided Dean when they were together but now with Dean coming to him, he didn’t exactly know how to proceed. He never once figured Dean would want to spend time with him. Was there a chance that Dean liked him? Maybe even in the same way that Castiel liked Dean? There had to be some kind of chance for Dean had traveled all this way apparently just for him.

“Alright.” 

“Alright?” Dean questioned back as he perked up a little up in excitement. 

“Yes, what you suggest is alright. I would enjoy to see what you have in mind.” Cas replied as he smiled over the rim of his glass before taking a sip. He was curious on what Dean could come up with.   
Maybe this time together would make them better friends as well. Cas secretly wished for more, but maybe this remaining vacation time with them together would give Castiel the confidence to ask Dean out when they got back home. 

~

The Florida trip had been nothing but a blast. Castiel couldn’t remember that last time he had laughed that much, let alone smiled or had fun. They had exchanged numbers before Dean had left to drive back. Not that they didn’t already have each other numbers from when they met back at Dean’s office. It was fine though now they had done the exchange officially and had been texting and calling ever since. 

Dean wanted more though. He wanted to take Cas on dates and kiss those gorgeous lips whenever he could. He had to just ask though. He needed to figure out how to ask and after weeks he finally figured it out. It was a risk though, Cas was either going to love his idea or absolutely hate it. 

It was Halloween and the whole library was decked out. The staff were all dressed up and they all agreed on the group costume set as a deck of cards. Charlie was, of course, the Queen. Meg claimed the Ace, while Anna took the King. No one else dared to fight the girls so each chose whatever card was left. All except Castiel. 

Cas was forced into the jester role. 

He didn’t necessarily mind wearing the get up but he didn’t quite understand why the three had pushed it on him. It at least didn’t have one of those ridiculous hats. It just had a green shawl for his shoulders that had a hood and bells attached to the ends. There was a red and gray tunic with more bells and then brown pants to finish it off. 

Cas was just thankful it was comfortable. The kids loved it. He was in the children’s section today reading Origins of Halloween books to all the kids that showed up. Groups upon groups had flocked to him, regulars of the library and newcomers as well. 

What was hilarious was that most of the parents that had brought those kids were mothers. Char, Anna, and Meg shared a laugh as the ladies fawned and tried to not so subtly flirt with Cas. 

“He’s here.” Charlie nearly squealed out as she looked down at the text she just received. 

“Chill queenie. Don’t have an aneurysm quite yet.” Meg chuckled though she was just as excited as Charlie. She wanted to see her unicorn happy and she knew Dean made him so. 

“Ah, here he comes.” Anna whispered as Dean walked up to them quickly and quietly as he could. 

“You forgot the crown, handmaiden.” Charlie whined but Dean rolled his eyes. 

“I told you no. This is embarrassing enough.” Dean whispered back harshly as he fiddled with the bouquet in his hands. He was dressed as a prince with a green tunic that was embellished with a fancy stripe on the chest. He also had a black over coat that down to the back of his knees. The rest was black pants and boots. 

Charlie called it her Elvish prince costume, but Dean didn’t care. He only smiled since the green he was wearing just happened to match the green on Cas’s shoulders. Cas looked really good. He was sure they both felt ridiculous but at least they looked good. 

“Do you know what you’re going to say?” Charlie asked as she glanced over at where Cas was still reading to the kids. Cas’s back was to them and he was so into the reading that almost nothing was going to break that concentration. 

“Yeah, kinda, I just got to go over and do it.” Dean sighed as he too glanced at Cas but quickly looked back at the fake flowers in his hands. 

“Well then, Seacrest, go get him.” Meg chuckled, and Anna gave him a small shove forward. 

“You got this.” Anna added with an thumbs up. Dean looked at all three before nodding. He sighed out his nerves, clutched the bouquet and strutted up to the kid’s section. 

“In the fall, when the vines begin to dry and die…” Cas read from the page slowly and clearly. He definitely had a way to keep the kids entertained with his voice. “…it is harvest time. It usually takes eighty to one hundred and twenty days, depending on the variety, for a seed to grow into a ripened pumpkin. It is ready to pick if it feels hard on the…outside…and…” 

Castiel trailed off as the kids in front of him were trying to hide their giggles and laughs. They were snickering and whispering to one another. Cas doesn’t quite understand but as he glanced at the parents that were standing in the back only to find them the same way. They were covering their giggles politely at least. 

Everyone was also not truly looking at him but more so behind him. Was there something funny behind him? He put the book down and turned around looking over his shoulder. He nearly fell out of his chair in surprise. 

Dean was standing just behind him holding out a bouquet of what appeared to be paper roses wrapped in a blue ribbon. His face turned pink as he took in Dean’s get up. He looked immensely handsome in the tunic that brought out the gold in his green eyes. 

“De…Dean?” Dean ignored all the staring eyes, sucked in a deep breath, and turned on all his charm. He smirked widely and gazed lovingly down into Cas’s eyes. 

“I’ve come a long way from my foreign kingdom fore I’ve heard tale of a great jester and bard. His voice is legendary throughout the land I hear say. I’ve come all this way to see if the rumors hold true.” Cas smiled, shyly blushing as he could now hear some of the mothers out right chuckled at Dean’s display. 

If Dean could ignore them and put on this act so could he. Cas turned fully in his chair and placed the book on his lap. He clutched it in a loose grip as he glanced back at Dean with a smirk of his own. 

“And are they?” 

Dean lowered the flowers, his smirk melting into a seductive smile. His eyes even twinkled from the overhead lights. “Oh yes. You are everything I’ve heard of and more. Would you do me the honor of sharing a meal with me, dear jester?” 

“Say yes, Mr. Cas!” One girl in the audience squealed before her friend sitting next to her shushed her. The other kids laughed, as well as some of the parents, yet all Dean could focus on was the joyous smile that spread over Cas’s face. 

“What do you kids think? Should I say yes?” Castiel asked as he turned back to the kids, regrettably taking his eyes off Dean. 

“Yes, Mr. Cas.” They all replied in chorus, again some of the parents adding in their voices of approval. 

“Well then, I guess I should then…” Cas started as he turned back to Dean, “…but first, my queen?” 

“Yes, my fine jester?” Charlie called back in her queen voice that Dean recognized from their Larping adventures. She never missed an opportunity to be a royal. 

“May I travel with this King for a journey and a meal?” Cas questioned as he finally rose from the reading chair. 

“Of course, of course. Go forth you two and run amuck!” Charlie said over dramatically before coming over and taking the book from Cas’s hands. She then plopped down in the chair as if it were her own throne. 

“Then it appears I am free and it would be my honor, my lord, to join you.” 

“No, the honor is truly mine.” Dean said in the sappiest voice he had before taking Cas’s hand and kissing along the knuckles. Kids behind them squealed in disgust though there was laughter as well. 

They went quite once again when Charlie picked up where Cas had left off. Dean didn’t bother to listen as Castiel lead him to a door further away from the children’s section. Cas opened the marked employee door with his key and the two slipped inside the hidden hallway, giggling just like the kids. 

“Here, take these already.” Dean chuckled as Cas finally accepted the fake bouquet from him. Cas looked down at them lovingly and even brought them to his face to sniff. He hadn’t expected a smell but was caught off guard when he caught not only one scent but several. In fact, they were several familiar scents. 

“Dean, why do these smell like perfume?” 

“That’s because they’re covered in sample perfumes.” Dean grinned with a slight blush. He didn’t know how Cas was going to react to what he said next. 

“I made this out of those gossip magazines you hate and if they had perfume samples in them I tried to rub it on the paper I was using.” 

Cas was at first stunned in silence. As he looked back down at the paper roses in his hand, his face quickly melted into one of awe and wonder. He had gone on a rant to Dean about how he despised gossip magazines of any kind. He always loved saying, to anyone who would listen, on how those trash magazines were a total and absolute disgrace to society. He firmly believed they weren’t even worth the paper they were printed on and was never ashamed to say it.

Now for Dean to make such beauty with them, it touched him dearly. Dean must have used many of those things since this was such a big bouquet. 

“If ya don’t like them, they’re easy to-“ Dean was happily cut off as Cas leaned forward and sealed their mouths together. Dean chuckled as he kissed back while slipping his hand up Cas’ neck to his hair, tangling it in the black locks. Once they pulled away enough to gaze into each other’s eyes both were smiling as if drunk on love. 

“So, dinner?” 

“Yes, please.” 

The End.

**Notes for the Chapter:**

> Beta'd again by my wonderful friend hey_you_with_the_face http://archiveofourown.org/users/hey_you_with_the_face   
> Love you deary again thank you.   
> Now Dean's outfit is here https://m.armstreet.com/store/medieval-clothing/Medieval-fantasy-costume-garb-cotton-brocade-coat-elven  
> And Cas's is here https://ulltotten.deviantart.com/art/Medieval-jester-outfit-204837884  
> And finally the Gif that inspired this fanfic all together can be found here https://ldrmas.tumblr.com/post/168176187476/round-the-usa-romance-gif-inspiration
> 
> Yes this whole fanfic was inspired by a Gif, do not judge.   
> I hope you all have enjoyed this story and if you did please leave a comment below! I would really like to hear from you guys.   
> I hope to see you all next time and now I will go celebrate my b-day.   
> Have a good one, everypony!


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